Sulfuric Acid → 1-(4-Chlorophenyl)-4-oxocyclohexanecarbonitrile

HRID 543854Notes

Reaction equation

HRID 543854 reaction equation
C([CH:5]1[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)([C:11]#[N:12])[CH2:8][CH2:7][C:6]1=[O:20])(OC)=O.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:9]2([C:11]#[N:12])[CH2:8][CH2:7][C:6](=[O:20])[CH2:5][CH2:10]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 122302342-Carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone

Product 1

HCID 122302381-(4-Chlorophenyl)-4-oxocyclohexanecarbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture consisting of 29.8 gm. (0.102 mole) of 2-carbomethoxy-4-(p-chlorophenyl)-4-cyanocyclohexanone (prepared in Part b, above), 550 ml. glacial acetic acid, and 330 ml. 10 percent sulfuric acid is heated on a steam bath at about 100° C. for 24 hours. The mixture is stirred continuously. After cooling, the mixture is diluted with 1000 ml. water, and extracted with benzene. The benzene phase is recovered and washed successively with water, with aqueous sodium bicarbonate, and with brine. The benzene is then removed by evaporation under reduced pressure to give a solid residue. The solid residue is recrystallized from diethyl ether to give 12.13 gm. (82% yield) of 4-(p-chlorophenyl)-4-cyanocyclohexanone having a melting point at 94.5° to 97° C.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is diluted with 1000 ml
  3. extractionwater, and extracted with benzene
  4. customThe benzene phase is recovered
  5. washwashed successively with water, with aqueous sodium bicarbonate
  6. customThe benzene is then removed by evaporation under reduced pressure
  7. customto give a solid residue
  8. customThe solid residue is recrystallized from diethyl ether
  9. customto give 12.13 gm

Sources & evidence

ORD record
ord-f6941548844a4f5ebd2cf05eba77fcb0
Source dataset
uspto-grants-1984_05
Patent number
US04447454

Reaction notes

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